US3714174A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Manufacture of bipyridylium salts
Assignee: Imperial Chemical Industries Ltd
•
Filing: 1969-12-05
•
Granted: 1973-01-30
•
Expires: 1989-12-05
Abstract
Abstract A process for the manufacture of a 1,1''-disubstituted-4,4''bipyridylium salt which comprises treating the corresponding 1,1''-disubstituted-1,1'',4,4''-tetrahydro-4,4''-bipyridyl with an organic compound which has a redox potential in water more positive than -1.48 volts as compared with the saturated calomel electrode and which reacts with a hydride ion with the formation of an anion which under the conditions of the reaction has a redox potential more positive than -0.45 volt as compared with the saturated calomel electrode.
Inventors
- 👤 J Colchester
- 👤 J Carey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:41
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/22
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
155 words
A process for the manufacture of a 1,1'' lower alkyl or carbamido lower alkyl-disubstituted -4,4''-bipyridylium salt which comprises treating at 20*C to 80*C the corresponding 1,1''-disubstituted-1,1''-4,4''-tetrahydro-4,4''-bipyridyl with an organic oxidizing agent which has a redox potential in water more positive than -1.48 volts as compared with the saturated calomel electrode and which reacts with a hydride ion removed from the said tetrahydrobipyridyl to form a stable anion which under the conditions of the reaction has a redox potential more positive than -0.45 volt as compared with the saturated calomel electrode, said oxidizing agent being selected from the group consisting essentially of alloxan, alloxan monohydrate, riboflavin, p-quinone dioxime, benzal barbituric acid, isatin, indane trione, methyl red, methyl violet, N-benzyl-3-carbamido-pyridinium chloride, malachite green, methylene blue, triphenyl-2,4,6,-pyrylium chloroferrate, N-methyl maleimide, phthalimide, phenolphthalein, M-methyl phenazonium methosulphate, 2,6-diphenyl pyrylium chloroferrate, N-benzyl nicotinamide chloride, m-dinitrobenzene and beta-nitrostyrene, the said oxidizing agent and bipyridyl being dissolved in an inert organic solvent therefor.
Claim 2
Dependent Claim
155 words
A process for the manufacture of a 1,1'' lower alkyl or carbamido lower alkyl-disubstituted -4,4''-bipyridylium salt which comprises treating at 20*C to 80*C the corresponding 1,1''-disubstituted-1,1''-4,4''-tetrahydro-4,4''-bipyridyl with an organic oxidizing agent which has a redox potential in water more positive than -1.48 volts as compared with the saturated calomel electrode and which reacts with a hydride ion removed from the said tetrahydrobipyridyl to form a stable anion which under the conditions of the reaction has a redox potential more positive than -0.45 volt as compared with the saturated calomel electrode, said oxidizing agent being selected from the group consisting essentially of alloxan, alloxan monohydrate, riboflavin, p-quinone dioxime, benzal barbituric acid, isatin, indane trione, methyl red, methyl violet, N-benzyl-3-carbamido-pyridinium chloride, malachite green, methylene blue, triphenyl-2,4,6,-pyrylium chloroferrate, N-methyl maleimide, phthalimide, phenolphthalein, M-methyl phenazonium methosulphate, 2,6-diphenyl pyrylium chloroferrate, N-benzyl nicotinamide chloride, m-dinitrobenzene and beta-nitrostyrene, the said oxidizing agent and bipyridyl being dissolved in an inert organic solvent therefor.
Claim 3
Dependent Claim
14 words
A process as claimed in claim 1 wherein the temperature is less than 100*C.
Claim 4
Dependent Claim
28 words
A process as claimed in claim 1 wherein the tetrahydrobipyridyl is employed in the form of a solution in which its concentration is about 0.5 mole per liter.
Claim 5
Dependent Claim
30 words
A process as claimed in claim 1 wherein the organic oxidizing agent is employed in the form of a solution in which its concentration is about 0.5 mole per liter.
Claim 6
Dependent Claim
23 words
A process as claimed in claim 1 wherein the molar ratio of the organic oxidizing agent to the tetrahydrobipyridyl is at least 2:1.
Claim 7
Dependent Claim
17 words
A process as claimed in claim 1 wherein the N-substituents of the tetrahydrobipyridyl are lower alkyl groups.
Claim 8
Dependent Claim
18 words
A process as claimed in claim 1 wherein the alkyl groups contain from one to six carbon atoms.
Claim 9
Dependent Claim
18 words
A process as claimed in claim 1 wherein the N-substitutents of the tetrahydrobipyridyl are carbamido lower alkyl groups.
Claim 10
Dependent Claim
16 words
A process as claimed in claim 1 wherein the said carbamidoalkyl groups are N,N-dialkyl carbamidomethyl groups.
References Cited (Backward Citations)
US3405135A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1976-01-30 | 1976-07-31 | 1977-01-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-01-30 | 1980-07-31 | 1981-01-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-01-30 | 1984-07-31 | 1985-01-30 | $7700.00 | Window Closed / Lapsed |